4-[(6-Chloropyridazin-3-yl)oxy]benzaldehyde synthesis

Yield:437383-95-4 86%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide; for 1 h;Heating / reflux;

Steps:

6 3-Chloro-6-(4-formylphenoxy)pyridazine

3-Chloro-6-(4-formylphenoxy)pyridazine 3,6-Dichloropyridazine (3.00g, 20.1mmol), 4-hydroxybenzaldehyde (2.46g, 20.1mmol), potassium carbonate (2.78g, 20.1 mmol) and 60mL of N,N-dimethylformamide were mixed and the mixture was refluxed for 1 hour. The reaction mixture was poured into water, which was extracted with ethyl acetate. The extracted solution was washed with brine, then dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:1v/v) to obtain 4.06g (86%) of the title compound as colorless crystalline powder. ¹H-NMR (400MHz, CDCl₃) δ 7.25(1H,d,J=9.3Hz), 7.39(2H,d,J=8.8Hz), 7.56(1H,d,J=9.3Hz), 7.96(2H,d,J=8.8Hz), 10.01

References:

EP1348698,2003,A1 Location in patent:Page/Page column 26